SILOXANES - VERSATILE TEMPLATES FOR ACYCLIC STEREOCONTROL - SYNTHESIS OF THE C27-C33 SEGMENT OF RAPAMYCIN

被引:69
作者
HALE, MR [1 ]
HOVEYDA, AH [1 ]
机构
[1] BOSTON COLL,DEPT CHEM,CHESTNUT HILL,MA 02167
关键词
D O I
10.1021/jo00032a007
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Five-membered siloxane rings may be employed to relay asymmetry along an acyclic chain in an efficient manner. Application of this method to the synthesis of the C27-C33 segment of the immunosuppressant rapamycin is reported.
引用
收藏
页码:1643 / 1645
页数:3
相关论文
共 31 条
  • [1] SUBSTRATE-SPECIFICITY FOR THE HUMAN ROTAMASE FKBP - A VIEW OF FK506 AND RAPAMYCIN AS LEUCINE (TWISTED AMIDE) PROLINE MIMICS
    ALBERS, MW
    WALSH, CT
    SCHREIBER, SL
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (17) : 4984 - 4986
  • [2] PROBING IMMUNOSUPPRESSANT ACTION WITH A NONNATURAL IMMUNOPHILIN LIGAND
    BIERER, BE
    SOMERS, PK
    WANDLESS, TJ
    BURAKOFF, SJ
    SCHREIBER, SL
    [J]. SCIENCE, 1990, 250 (4980) : 556 - 559
  • [3] ON STEREOCHEMISTRY OF OSMIUM TETRAOXIDE OXIDATION OF ALLYLIC ALCOHOL SYSTEMS - EMPIRICAL RULE
    CHA, JK
    CHRIST, WJ
    KISHI, Y
    [J]. TETRAHEDRON, 1984, 40 (12) : 2247 - 2255
  • [4] ON STEREOCHEMISTRY OF OSMIUM-TETROXIDE OXIDATION OF ALLYLIC ALCOHOL SYSTEMS - EMPIRICAL RULE
    CHA, JK
    CHRIST, WJ
    KISHI, Y
    [J]. TETRAHEDRON LETTERS, 1983, 24 (37) : 3943 - 3946
  • [5] STEREOSELECTIVE OSMYLATION OF 1,1-DISUBSTITUTED OLEFINS - EFFECT OF ALLYLIC SUBSTITUENTS ON REACTION DIASTEREOSELECTIVITY
    EVANS, DA
    KALDOR, SW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) : 1698 - 1700
  • [6] ON THE CHEMISTRY AND HIGH-FIELD NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY OF RAPAMYCIN
    FINDLAY, JA
    RADICS, L
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1980, 58 (06): : 579 - 590
  • [7] SYNTHETIC STUDIES TOWARD RAPAMYCIN - A SOLUTION TO A PROBLEM IN CHIRALITY MERGER THROUGH USE OF THE IRELAND REACTION
    FISHER, MJ
    MYERS, CD
    JOGLAR, J
    CHEN, SH
    DANISHEFSKY, SJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) : 5826 - 5834
  • [8] FISHER MJ, 1991, J ORG CHEM, V56, P5834
  • [9] RAPAMYCIN AND FK506 BINDING-PROTEINS (IMMUNOPHILINS)
    FRETZ, H
    ALBERS, MW
    GALAT, A
    STANDAERT, RF
    LANE, WS
    BURAKOFF, SJ
    BIERER, BE
    SCHREIBER, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (04) : 1409 - 1411
  • [10] GOULET MT, 1990, TETRAHEDRON LETT, V31, P4845